EP0335115B1 - Pharmazeutische und kosmetische Zusammensetzungen auf der Basis von Benzoylperoxid und quaternären Ammoniumsalzen - Google Patents
Pharmazeutische und kosmetische Zusammensetzungen auf der Basis von Benzoylperoxid und quaternären Ammoniumsalzen Download PDFInfo
- Publication number
- EP0335115B1 EP0335115B1 EP89103375A EP89103375A EP0335115B1 EP 0335115 B1 EP0335115 B1 EP 0335115B1 EP 89103375 A EP89103375 A EP 89103375A EP 89103375 A EP89103375 A EP 89103375A EP 0335115 B1 EP0335115 B1 EP 0335115B1
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- European Patent Office
- Prior art keywords
- composition according
- denotes
- quaternary ammonium
- composition
- radical
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 239000004342 Benzoyl peroxide Substances 0.000 title claims abstract description 18
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 235000019400 benzoyl peroxide Nutrition 0.000 title claims abstract description 18
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 10
- -1 quaternary ammonium alkyl sulphates Chemical class 0.000 claims abstract description 23
- 238000011282 treatment Methods 0.000 claims abstract description 20
- 230000000699 topical effect Effects 0.000 claims abstract description 8
- 239000002537 cosmetic Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 4
- 206010000496 acne Diseases 0.000 claims description 16
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 14
- 150000003254 radicals Chemical class 0.000 claims description 11
- 208000017520 skin disease Diseases 0.000 claims description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 5
- 239000000499 gel Substances 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- QDYLMAYUEZBUFO-UHFFFAOYSA-N cetalkonium chloride Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 QDYLMAYUEZBUFO-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- NVQYHXBJMIDJDG-UHFFFAOYSA-N 1-hexadecoxypyridin-1-ium Chemical compound CCCCCCCCCCCCCCCCO[N+]1=CC=CC=C1 NVQYHXBJMIDJDG-UHFFFAOYSA-N 0.000 claims description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- HACQADBEBRDLMC-UHFFFAOYSA-N N-cyclohexyl-N-(2-methylheptadecan-2-yl)hydroxylamine Chemical compound CCCCCCCCCCCCCCCC(C)(C)N(C1CCCCC1)O HACQADBEBRDLMC-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000000058 anti acne agent Substances 0.000 claims description 2
- 229940124340 antiacne agent Drugs 0.000 claims description 2
- NEUSVAOJNUQRTM-UHFFFAOYSA-N cetylpyridinium Chemical compound CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NEUSVAOJNUQRTM-UHFFFAOYSA-N 0.000 claims description 2
- 229960004830 cetylpyridinium Drugs 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- UENRCAFKOCYSLM-UHFFFAOYSA-N hexadecyl-(2-hydroxyethyl)-dimethylazanium Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)CCO UENRCAFKOCYSLM-UHFFFAOYSA-N 0.000 claims description 2
- 235000013336 milk Nutrition 0.000 claims description 2
- 210000004080 milk Anatomy 0.000 claims description 2
- 239000002674 ointment Substances 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- 239000000516 sunscreening agent Substances 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims 3
- DCLKMMFVIGOXQN-UHFFFAOYSA-N 1-hexadecyl-3-methylimidazol-3-ium Chemical compound CCCCCCCCCCCCCCCCN1C=C[N+](C)=C1 DCLKMMFVIGOXQN-UHFFFAOYSA-N 0.000 claims 1
- HEAATPJLXOZNPZ-UHFFFAOYSA-N 12-methoxy-N,N-dimethyldodecan-1-amine Chemical compound COCCCCCCCCCCCCN(C)C HEAATPJLXOZNPZ-UHFFFAOYSA-N 0.000 claims 1
- 206010040943 Skin Ulcer Diseases 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- OXVLUGWXMOZHLG-UHFFFAOYSA-N dimethyl-[2-(2-phenoxyethoxy)ethyl]-(9-phenylnonyl)azanium Chemical compound C[N+](CCOCCOC1=CC=CC=C1)(CCCCCCCCCC1=CC=CC=C1)C OXVLUGWXMOZHLG-UHFFFAOYSA-N 0.000 claims 1
- 239000008267 milk Substances 0.000 claims 1
- 231100000019 skin ulcer Toxicity 0.000 claims 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 abstract description 4
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 6
- 239000003242 anti bacterial agent Substances 0.000 description 6
- 229940088710 antibiotic agent Drugs 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000001530 keratinolytic effect Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229940124091 Keratolytic Drugs 0.000 description 3
- 208000025865 Ulcer Diseases 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229960003276 erythromycin Drugs 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- ORIZJEOWAFVTGA-UHFFFAOYSA-N 1-hexadecylimidazole Chemical compound CCCCCCCCCCCCCCCCN1C=CN=C1 ORIZJEOWAFVTGA-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000002995 comedolytic effect Effects 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-O propan-1-aminium Chemical compound CCC[NH3+] WGYKZJWCGVVSQN-UHFFFAOYSA-O 0.000 description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- ZRIILUSQBDFVNY-UHFFFAOYSA-N 4-dodecylmorpholine Chemical compound CCCCCCCCCCCCN1CCOCC1 ZRIILUSQBDFVNY-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 241000186427 Cutibacterium acnes Species 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- FEOXXRFIXJHGMS-UHFFFAOYSA-N N-benzyl-N-[2-methyl-2-(2-phenoxyethoxy)propyl]octan-1-amine Chemical compound CCCCCCCCN(CC1=CC=CC=C1)CC(C)(C)OCCOC2=CC=CC=C2 FEOXXRFIXJHGMS-UHFFFAOYSA-N 0.000 description 1
- RGJIAIUKHJXQRV-UHFFFAOYSA-N O[S](C1CCC1)(c1ccccc1)(=O)=O Chemical compound O[S](C1CCC1)(c1ccccc1)(=O)=O RGJIAIUKHJXQRV-UHFFFAOYSA-N 0.000 description 1
- ORNBQBCIOKFOEO-YQUGOWONSA-N Pregnenolone Natural products O=C(C)[C@@H]1[C@@]2(C)[C@H]([C@H]3[C@@H]([C@]4(C)C(=CC3)C[C@@H](O)CC4)CC2)CC1 ORNBQBCIOKFOEO-YQUGOWONSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 230000003255 anti-acne Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
- 229960001950 benzethonium chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- XIWFQDBQMCDYJT-UHFFFAOYSA-M benzyl-dimethyl-tridecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 XIWFQDBQMCDYJT-UHFFFAOYSA-M 0.000 description 1
- KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 description 1
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 1
- 229940000635 beta-alanine Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229960000228 cetalkonium chloride Drugs 0.000 description 1
- 229960001927 cetylpyridinium chloride Drugs 0.000 description 1
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 1
- 229960002227 clindamycin Drugs 0.000 description 1
- KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- VCSZKKITTDFXQJ-UHFFFAOYSA-N dodecyl-methoxy-dimethylazanium Chemical compound CCCCCCCCCCCC[N+](C)(C)OC VCSZKKITTDFXQJ-UHFFFAOYSA-N 0.000 description 1
- VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical compound CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- MFLMYFVIROLIRS-UHFFFAOYSA-M hexadecyl-(2-hydroxycyclohexyl)-dimethylazanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C1CCCCC1O MFLMYFVIROLIRS-UHFFFAOYSA-M 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000003410 keratolytic agent Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940127249 oral antibiotic Drugs 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229960000249 pregnenolone Drugs 0.000 description 1
- OZZAYJQNMKMUSD-DMISRAGPSA-N pregnenolone succinate Chemical compound C1C=C2C[C@@H](OC(=O)CCC(O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 OZZAYJQNMKMUSD-DMISRAGPSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229940055019 propionibacterium acne Drugs 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/14—Quaternary ammonium compounds, e.g. edrophonium, choline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/38—Percompounds, e.g. peracids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
Definitions
- the present invention relates to pharmaceutical and cosmetic compositions based on benzoyl peroxide and quaternary ammonium salts and their use, especially for the treatment of acne.
- the etiopathology of acne although poorly defined, originates in the formation of a characteristic lesion: the comedo. This results from obstruction of the pilosebaceous canal as a result of dyskeratinization of the infundibulum zone of the canal. The main effect of the obstruction is hyperproliferation of the resident skin strains, which then triggers an inflammatory reaction of the body.
- benzoyl peroxide has proved for many years to be a particularly interesting keratolytic agent, further having good bacteriostatic properties.
- benzoyl peroxide was then combined with the antibiotics.
- the latter has, in particular, been associated with erythromycin (FR-A-2378523).
- antibiotics associated or not with benzoyl peroxide have the major disadvantage during prolonged use, to make the bacterial flora resistant. They become less active during subsequent treatments. (LEYDEN JJ, J. Am Acad Dermatol 8 (1) 41-45 (1983)).
- Stable detergent compositions possibly used for the cleaning of the bit, which can contain simultaneously a quaternary ammonium surfactant such as benzalkonium chloride, cetalkonium chloride, cetylpyridinium chloride, benzethonium chloride or cethexonium bromide and benzoyl peroxide (FR-A-2328039).
- a quaternary ammonium surfactant such as benzalkonium chloride, cetalkonium chloride, cetylpyridinium chloride, benzethonium chloride or cethexonium bromide and benzoyl peroxide (FR-A-2328039).
- the Applicant has just discovered, quite surprisingly, that it is possible to obtain stable compositions in the treatment of acne, cutaneous ulcer, and generally in the treatment of dermatoses and skin disorders. , by associating benzoyl peroxide with certain quaternary ammonium derivatives.
- benzoyl peroxide can be used at low doses, with the advantage of improving skin tolerance.
- compositions according to the invention are well tolerated by the body. They have very good antibacterial properties, without inducing resistance of strains, they are keratolytic, bacteriostatic, especially vis-à-vis Propionibacterium Acnes which is one of the main germs responsible for acne and are active in treatment and reduction of the number of comedones.
- compositions according to the invention are suitable for the treatment of cutaneous disorders and dermatoses, such as, in particular, acne and cutaneous ulcer.
- the present invention therefore relates to a topical pharmaceutical and / or cosmetic composition containing benzoyl peroxide and at least one quaternary ammonium salt such as those described below.
- the invention also relates to a cosmetic treatment method implementing such an association.
- composition intended for a topical application in accordance with the invention is essentially characterized in that it contains, in a physiologically acceptable medium, benzoyl peroxide and a quaternary ammonium salt chosen from alkyl sulphates or sulphonates, aryl sulphonates and quaternary ammonium alkyl aryl sulfonates.
- X ⁇ denotes an alkyl sulphate or sulphonate anion, aryl sulphonate or alkyl aryl sulphonate.
- Particularly preferred anions are chosen from the anions of the following formulas:
- compositions may be in the form of solutions, emulsions, suspensions, gels or dispersions, containing at least one compound corresponding to formula (I) in concentrations of between 0.01 and 25% by weight, relative to the total weight of the composition and preferably between 0.1 and 5% by weight and benzoyl peroxide in concentrations of between 0.1 and 20% by weight relative to the total weight of the composition and preferably included between 0.5 and 10% by weight.
- compositions in accordance with the invention may also contain foaming or emulsifying surfactants, polymers such as cellulose and its derivatives, guar gum, heterobiopolysaccharides, polyacrylic acids and their derivatives, poly- ⁇ -alanine, ethers or esters of polyethylene glycols, colloidal silica, superfatting agents, emollients, wetting agents, pH regulators, penetration agents, preservatives, sunscreens, perfumes, dyes and / or pigments having as their function of coloring the skin or the composition itself and any other ingredient usually used in compositions intended for topical application.
- foaming or emulsifying surfactants polymers such as cellulose and its derivatives, guar gum, heterobiopolysaccharides, polyacrylic acids and their derivatives, poly- ⁇ -alanine, ethers or esters of polyethylene glycols, colloidal silica, superfatting agents, emollients, wetting agents, pH regulators, penetration agents, preservatives
- the galenic forms mainly conditioned for the topical route are especially in the form of solutions, creams, milks, gels, dispersions or microemulsions more or less thickened, soaked swabs, ointments, sticks or in the form of soap bars.
- Another subject of the invention is therefore also constituted by the use of pharmaceutical compositions for the preparation of a medicament for the treatment of dermatoses, such as, in particular, acne, cutaneous ulcers, warts and dyskeratinizations of the skin. skin.
- dermatoses such as, in particular, acne, cutaneous ulcers, warts and dyskeratinizations of the skin. skin.
- compositions in accordance with the invention, may be used for the cosmetic treatment of the skin, especially as a cleaning and disinfecting, comedolytic, keratolytic product.
- Another object of the invention relates to a cosmetic treatment process characterized in that it consists in applying to the skin a composition according to the invention for purifying or purifying the latter.
- This composition is used as a skin cream once or twice a day for one to twelve weeks.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
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Claims (18)
1. Zusammensetzung zur topischen Anwendung, dadurch gekennzeichnet, dass sie in einem physiologisch akzeptablen Milieu Benzoylperoxid und ein quartäres Ammoniumsalz umfasst, ausgewählt aus den quartären Ammoniumsalzen von Alkylsulfaten oder -sulfonaten, Arylsulfonaten und den Alkylarylsulfonaten.
2. Zusammensetzung nach Anspruch 1, dadurch gekennzeichnet, dass das quartäre Ammoniumsalz durch die folgende allgemeine Formel (I) dargestellt ist:
worin bedeuten:
(i) R₁ eine Gruppe 
worin bedeuten: 
worin bedeuten:
0 ≦ n ≦ 6 und p bedeutet 0 oder 1;
R bedeutet ein Alkylradikal, ein Alkylcycloalkylradikal oder Alkylarylradikal mit 8 bis 32 C-Atomen, wobei die aliphatische Kette gegebenenfalls durch eine Ether-, Amid-, Sulfonamid- oder Carbamatgruppe unterbrochen sein kann und/oder einen Hydrokylsubstituenten tragen kann;
wenn n von 0 unterschiedlich ist, bedeutet Z H, CH₃ oder CH₂OH;
wenn Z H oder CH₃ bedeutet, ist p gleich 0;
wenn Z CH₂OH bedeutet, ist p gleich 1;
die Gruppe (OC₂H₃Z) kann die eine oder die andere der nachfolgenden Verknüpfungen aufweisen:
wenn n von 0 unterschiedlich ist, bedeutet Z H, CH₃ oder CH₂OH;
wenn Z H oder CH₃ bedeutet, ist p gleich 0;
wenn Z CH₂OH bedeutet, ist p gleich 1;
die Gruppe (OC₂H₃Z) kann die eine oder die andere der nachfolgenden Verknüpfungen aufweisen:
(ii) R₂ bedeutet ein C₁₋₂₂-Alkylradikal, welches gegebenenfalls eine oder mehrere Hydrokylgruppen umfassen kann;
(iii) R₃ bedeutet ein C₁₋₆-Alkylradikal, ein C₁₋₆-Monohydrokyalkylradikal, ein C₃₋₆-Polyhydrokyalkylradikal oder ein Benzylradikal;
(iv) R₄ bedeutet ein Alkyl- oder Alkyloxyradikal mit 1 bis 18 C-Atomen;
(v) R₂ und R₃ können zusammen mit dem Stickstoffatom einen Heterozyklus, wie das Piperidin oder Morpholin bilden; oder
(vi) R₁, R₂ und R₃ können mit dem Stickstoffatom einen Pyridin-, Methylpyridin- oder Hydrokypyridinring bilden;
X⁻ bedeutet ein Alkylsulfat- oder -sulfonat-, Arylsulfonat- oder Alkylarylsulfonat-anion.
X⁻ bedeutet ein Alkylsulfat- oder -sulfonat-, Arylsulfonat- oder Alkylarylsulfonat-anion.
3. Zusammensetzung nach Anspruch 2, dadurch gekennzeichnet, dass das Anion X⁻ aus den Gruppen mit den folgenden Formeln ausgewählt ist:
oder
4. Zusammensetzung nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass das quartäre Ammoniumsalz, welches durch die allgemeine Formel (I) dargestellt ist, ausgewählt ist aus Trimethyl-laurylammonium, Dimethyl-hydroxyethyl-cetylammonium, Dimethyl-methoxy-laurylammonium, Trimethyl-laurylamido-propylammonium, Cetylpyridinium, Cetyloxypyridinium, Dimethyl-benzyl-cetylammonium, Dimethyl-benzyl-octylphenory-ethoxyethylammonium, Dimethyl-hydroxycyclohexyl-cetylammonium, N-Methyl-, N-Cetylimidazolium- oder Methyllauryl-morpholinium.
5. Zusammensetzung nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass das Benzoylperoxid in einer Menge von 0,1 bis 20 Gew.%, bezogen auf das Gesamtgewicht der Zusammensetzung, vorhanden ist.
6. Zusammensetzung nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass das quartäre Ammoniumsalz der allgemeinen Formel (I) in einer Menge von 0,01 bis 25 Gew.%, bezogen auf das Gesamtgewicht der Zusammensetzung, vorhanden ist.
7. Zusammensetzung nach Anspruch 5, dadurch gekennzeichnet, dass das Benzoylperoxid in einer Menge von 0,5 bis 10 Gew.%, bezogen auf das Gesamtgewicht der Zusammensetzung, vorhanden ist.
8. Zusammensetzung nach Anspruch 6, dadurch gekennzeichnet, dass das quartäre Ammoniumsalz der allgemeinen Formel (I) in einer Menge von 0,1 bis 5 Gew.%, bezogen auf das Gesamtgewicht der Zusammensetzung, vorhanden ist.
9. Zusammensetzung nach einem der Ansprüche 1 bis 8 zur Anwendung als Medikament, dadurch gekennzeichnet, dass der geeignete Träger ein pharmazeutisch akzeptabler Träger ist.
10. Zusammensetzung nach einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, dass der geeignete Träger ein kosmetisch akzeptabler Träger ist.
11. Zusammensetzung nach einem der Ansprüche 1 bis 10, dadurch gekennzeichnet, dass sie in Form von Gelen, Lösungen, Dispersionen, Emulsionen oder Suspensionen vorliegt.
12. Zusammensetzung nach einem der Ansprüche 1 bis 11, dadurch gekennzeichnet, dass sie in Form einer Creme, einer Milch, eines Gels, eines imprägnierten Tupfers, einer Pommade, eines Stiftes oder in Form eines Stückes Seife vorhanden ist.
13. Zusammensetzung nach einem der Ansprüche 1 bis 12, dadurch gekennzeichnet, dass sie zusätzlich zumindest ein anderes Anti-Aknemittel enthält.
14. Zusammensetzung nach einem der Ansprüche 1 bis 13, dadurch gekennzeichnet, dass sie zusätzlich zumindest einen Sonnenfilter enthält.
15. Verwendung der Zusammensetzungen nach Anspruch 9 zur Herstellung eines Medikamentes zur Behandlung von Dermatosen.
16. Verwendung der Zusammensetzungen nach Anspruch 15 zur Behandlung von ulzeröser Haut, von Warzen und Dyskeratose der Haut.
17. Verwendung der Zusammensetzungen nach Anspruch 9 zur Herstellung eines Medikamentes zur Behandlung von Akne.
18. Verfahren zur kosmetischen Behandlung, gekennzeichnet durch Auftragung einer Zusammensetzung, wie sie in Anspruch 10 definiert ist, auf die Haut, um die Haut zu reinigen und zu säubern.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT89103375T ATE69162T1 (de) | 1988-03-09 | 1989-02-27 | Pharmazeutische und kosmetische zusammensetzungen auf der basis von benzoylperoxid und quaternaeren ammoniumsalzen. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8803042A FR2628319B1 (fr) | 1988-03-09 | 1988-03-09 | Compositions pharmaceutiques et cosmetiques a base de peroxyde de benzoyle et de sels d'ammonium quaternaires |
| FR8803042 | 1988-03-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0335115A2 EP0335115A2 (de) | 1989-10-04 |
| EP0335115A3 EP0335115A3 (en) | 1989-10-18 |
| EP0335115B1 true EP0335115B1 (de) | 1991-11-06 |
Family
ID=9364094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP89103375A Expired - Lifetime EP0335115B1 (de) | 1988-03-09 | 1989-02-27 | Pharmazeutische und kosmetische Zusammensetzungen auf der Basis von Benzoylperoxid und quaternären Ammoniumsalzen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4960772A (de) |
| EP (1) | EP0335115B1 (de) |
| JP (1) | JP2689991B2 (de) |
| AT (1) | ATE69162T1 (de) |
| CA (1) | CA1339085C (de) |
| DE (1) | DE68900402D1 (de) |
| FR (1) | FR2628319B1 (de) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995023587A1 (en) * | 1994-03-03 | 1995-09-08 | The Procter & Gamble Company | Anti-acne compositions |
| DE19640205A1 (de) | 1996-09-30 | 1998-04-02 | Bayer Ag | Wasserdispergierbare Isocyanate mit verbessertem Aufziehvermögen als Papierhilfsmittel |
| DE19809669A1 (de) | 1998-03-06 | 1999-09-09 | Bayer Ag | Wasserdispergierbare Polyisocyanatzubereitungen zur Herstellung von wiederaufschließbarem Papier |
| US7758888B2 (en) | 2000-04-21 | 2010-07-20 | Sol-Gel Technologies Ltd. | Composition exhibiting enhanced formulation stability and delivery of topical active ingredients |
| US7820186B2 (en) | 2001-12-21 | 2010-10-26 | Galderma Research & Development | Gel composition for once-daily treatment of common acne comprising a combination of benzoyl peroxide and adapalene and/or adapalene salt |
| FR2833841B1 (fr) * | 2001-12-21 | 2005-07-22 | Galderma Res & Dev | Gel comprenant au moins un retinoide et du peroxyde de benzoyle |
| US6783767B2 (en) | 2002-02-08 | 2004-08-31 | Healthpoint, Ltd. | Low temperature disinfectant/sterilant for medical devices and topical applications |
| BR0314345A (pt) * | 2002-09-04 | 2005-07-26 | Lonza Ag | Lubrificante antimicrobiano para compósitos de madeira fibra-plástica |
| US7776355B2 (en) * | 2003-07-03 | 2010-08-17 | Medics Pharmaceutical Corporation | Delivery system for topical medications |
| US20050025817A1 (en) * | 2003-07-03 | 2005-02-03 | Bhatia Kuljit S. | Delivery system for topical medications |
| US7479289B2 (en) * | 2004-07-02 | 2009-01-20 | Medicis Pharmaceutical Corporation | Stable cleanser compositions containing sulfur |
| US7655682B2 (en) * | 2004-07-02 | 2010-02-02 | Medicis Pharmaceutical Corporation | Triple anti-irritant composition |
| MX2007010881A (es) * | 2005-03-10 | 2007-12-05 | Jr Chem Llc | Composiciones de peroxido de benzoilo y metodos de uso. |
| CA2600762C (en) * | 2005-03-10 | 2011-05-31 | Jr Chem, Llc | Stable organic peroxide compositions |
| US7556820B2 (en) | 2005-06-29 | 2009-07-07 | Jr Chem, Llc | Stable organic peroxide compositions |
| US20090306023A1 (en) * | 2005-06-29 | 2009-12-10 | Ramirez Jose E | Stable organic peroxide compositions |
| WO2007002880A2 (en) * | 2005-06-29 | 2007-01-04 | Jr Chem, Llc | Method of enhanced drug application |
| US20070001145A1 (en) * | 2005-06-29 | 2007-01-04 | Faryniarz Joseph R | Stable organic peroxide compositions |
| WO2007015243A2 (en) * | 2005-08-02 | 2007-02-08 | Sol-Gel Technologies Ltd. | Metal oxide coating of water insoluble ingredients |
| BRPI0709674A2 (pt) | 2006-03-31 | 2011-12-06 | Stiefel Res Australia Pty Ltd | gel de suspensão espumante |
| FR2910321B1 (fr) | 2006-12-21 | 2009-07-10 | Galderma Res & Dev S N C Snc | Gel creme comprenant au moins un retinoide et du peroxyde de benzole |
| MX2009008250A (es) | 2007-02-01 | 2009-08-27 | Sol Gel Technologies Ltd | Composiciones para aplicacion topica que comprenden un peroxido y retinoide. |
| US20100226948A1 (en) | 2009-03-05 | 2010-09-09 | Medicis Pharmaceutical Corporation | Methods and compositions for treating acne |
| WO2013124820A1 (en) | 2012-02-21 | 2013-08-29 | Ranbaxy Laboratories Limited | Composition comprising a retinoid and benzoyl peroxide |
| US9687465B2 (en) | 2012-11-27 | 2017-06-27 | Sol-Gel Technologies Ltd. | Compositions for the treatment of rosacea |
| WO2017029665A1 (en) | 2015-08-20 | 2017-02-23 | Sol-Gel Technologies Ltd. | Compositions for topical application comprising benzoyl peroxide and adapalene |
| JP2020527143A (ja) * | 2017-07-12 | 2020-09-03 | ソル − ゲル テクノロジーズ リミテッド | ざ瘡の治療のための方法および組成物 |
| JPWO2022118942A1 (de) * | 2020-12-04 | 2022-06-09 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2852434A (en) * | 1953-08-28 | 1958-09-16 | Chesebrough Ponds | Nu-soya nu-ethyl morpholinium ethosulfate cosmetic emulsions |
| US2865805A (en) * | 1954-05-04 | 1958-12-23 | Gallowhur Chemical Corp | Quaternary ammonium naphthalene and naphthol sulfonates |
| GB1163044A (en) * | 1966-03-30 | 1969-09-04 | Stiefel Laboratories | Improvements in Therapeutic Composition. |
| US3890227A (en) * | 1971-09-22 | 1975-06-17 | Petro Tex Chem Corp | Treatment of process water |
| US3852210A (en) * | 1972-08-11 | 1974-12-03 | Flow Pharma Inc | Stable liquid detergent concentrates containing active oxygen |
| US4167487A (en) * | 1973-06-07 | 1979-09-11 | Colgate-Palmolive Company | Aromatic activator |
| US3886278A (en) * | 1973-08-22 | 1975-05-27 | Mead Johnson & Co | Ammonium carboxylate sebum inhibition process |
| US4021572A (en) * | 1975-07-23 | 1977-05-03 | Scott Eugene J Van | Prophylactic and therapeutic treatment of acne vulgaris utilizing lactamides and quaternary ammonium lactates |
| FR2378523A1 (fr) * | 1977-01-26 | 1978-08-25 | Grupper Charles | Medicament pour le traitement de l'acne |
| US4361584A (en) * | 1977-10-07 | 1982-11-30 | A.H.C. Pharmacal, Inc. | Composition and method for the treatment of acne |
| US4387107A (en) * | 1979-07-25 | 1983-06-07 | Dermik Laboratories, Inc. | Stable benzoyl peroxide composition |
| GB2068228B (en) * | 1980-01-24 | 1984-02-29 | Janssen Pharmaceutica Nv | Anti-microbial compositions for the topical treatment of acne vulgaris |
| US4330551A (en) * | 1980-08-26 | 1982-05-18 | Synergetics Co. | Therapeutic method |
| US4692329A (en) * | 1980-12-08 | 1987-09-08 | William H. Rorer, Inc. | Erythromycin/benzoyl peroxide antiacne compositions |
| US4547305A (en) * | 1982-07-22 | 1985-10-15 | Lever Brothers Company | Low temperature bleaching detergent compositions comprising peracids and persalt activator |
| LU85111A1 (fr) * | 1983-12-01 | 1985-09-12 | Oreal | Composition anti-acnetique a base de peroxyde de benzoyle et d'au moins un filtre solaire |
| LU85746A1 (fr) * | 1985-01-28 | 1986-08-04 | Oreal | Composition cosmetique filtrante contenant un filtre uv associe a un polymere obtenu par polymerisation sequentielle en emulsion et son utilisation pour la protection de l'epiderme humain contre les radiations ultraviolettes |
| US4737307A (en) * | 1986-09-18 | 1988-04-12 | Brown Robert L | Skin cleanser capable of removing smegma and surface bacteria, fungus and viruses from surface of skin |
| FR2604435B1 (fr) * | 1986-09-30 | 1988-12-02 | Oreal | Peroxydes aromatiques insatures et leur utilisation en therapeutique et cosmetique |
| FR2604357B1 (fr) * | 1986-09-30 | 1988-12-02 | Oreal | Composition pharmaceutique et cosmetique anti-acneique |
-
1988
- 1988-03-09 FR FR8803042A patent/FR2628319B1/fr not_active Expired - Fee Related
-
1989
- 1989-02-23 US US07/314,659 patent/US4960772A/en not_active Expired - Lifetime
- 1989-02-27 AT AT89103375T patent/ATE69162T1/de not_active IP Right Cessation
- 1989-02-27 EP EP89103375A patent/EP0335115B1/de not_active Expired - Lifetime
- 1989-02-27 DE DE8989103375T patent/DE68900402D1/de not_active Expired - Fee Related
- 1989-03-08 JP JP1053955A patent/JP2689991B2/ja not_active Expired - Fee Related
- 1989-03-09 CA CA000593265A patent/CA1339085C/fr not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4960772A (en) | 1990-10-02 |
| CA1339085C (fr) | 1997-07-29 |
| ATE69162T1 (de) | 1991-11-15 |
| DE68900402D1 (de) | 1991-12-12 |
| EP0335115A2 (de) | 1989-10-04 |
| FR2628319A1 (fr) | 1989-09-15 |
| JPH01268632A (ja) | 1989-10-26 |
| FR2628319B1 (fr) | 1990-12-07 |
| EP0335115A3 (en) | 1989-10-18 |
| JP2689991B2 (ja) | 1997-12-10 |
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